Isobutyl chloroformate → tert-Butyl ((1S,3R)-3-(hydroxymethyl)cyclohexyl)carbamate

HRID 1696208노트

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HRID 1696208 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](O)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[BH4-].[Na+].S([O-])(O)(=O)=O.[K+].C(=O)([O-])O.[Na+]>O1CCCC1.CO.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([CH2:15][OH:16])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

9

반응물 5

HCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 2755995rel-(1R,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acidHCID 4311764Sodium borohydride

생성물 1

HCID 83823767tert-Butyl ((1S,3R)-3-(hydroxymethyl)cyclohexyl)carbamate수율 66%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

To a solution of cis-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylic acid (500 mg) in tetrahydrofuran (5 ml) was added triethylamine (344 μl) and isobutyl chloroformate (320 μl) under stirring at 0° C. After stirring at 0° C. for 1 hour, sodium borohydride (233 mg) was added, and methanol (5 ml) was added dropwise under stirring at 0° C. After stirring at 0° C. for 1 hour, 10% aqueous potassium hydrogen sulfate (10 ml) was added and neutralized with saturated aqueous sodium hydrogencarbonate. and extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane:EtOAc=70:30 to 40:60 to give tert-butyl[cis-3-(hydroxymethyl)cyclohexyl]carbamate (311 mg) as a white powder.

후처리

  1. stirringAfter stirring at 0° C. for 1 hour
  2. stirringunder stirring at 0° C
  3. stirringAfter stirring at 0° C. for 1 hour
  4. extractionand extracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane

출처 및 근거

ORD 기록
ord-48d8f1b2730f496891bef545b99a27f6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163767B2

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