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

HRID 1696208ノート

反応式

HRID 1696208 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-48d8f1b2730f496891bef545b99a27f6
出典データセット
uspto-grants-2012_04
特許番号
US08163767B2

反応ノート

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