tert-butyl 4-[3-(hydroxymethyl)phenyl]piperazine-1-carboxylate synthesis

6synthesis methods

Product Name:tert-butyl 4-[3-(hydroxymethyl)phenyl]piperazine-1-carboxylate
CAS Number:261925-88-6
Molecular formula:C16H24N2O3
Molecular Weight:292.37

4-[3-(METHOXYCARBONYL)PHENYL]-1-PIPERAZINECARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER

179003-10-2
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tert-butyl 4-[3-(hydroxymethyl)phenyl]piperazine-1-carboxylate

261925-88-6
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$502.88/5MG

Yield:261925-88-6 98.6%

Reaction Conditions:

with lithium borohydride in tetrahydrofuran at 20;Inert atmosphere;Cooling with ice;

Steps:

217 21 7C. tert-Butyl 4-(3-(hydroxymethyl)phenyl)piperazine- 1 -carboxylate

217B (171 mg, 0.534 mmol) was dissolved in THF (5.3 mL) and cooled in an ice bath with stirring under argon. A 2M solution of LiBH4 in THF (0.53 mL, 1.1 mmol)was added dropwise. The resulting pale yellow solution was stirred for 1 h in an ice bath, then overnight at a The reaction mixture was heated to reflux for 1 h, then cooled to 0 °C and quenched with 1M HC1 to pH 1. The mixture was stirred for 30 mm, then the pH was adjusted to 9-10 with solid K2C03. The mixture was extracted with EtOAc (2x). Thecombined extracts were washed with brine, dried over Na2SO4, filtered and evaporated togive 217C (154 mg, 98.6%) as a white solid. MS(ESI) m/z 292.9 (M+H).

References:

WO2017/40449,2017,A1 Location in patent:Paragraph 00524