Isobutyl chloroformate → HCID 83823767, compound

HRID 1696208Notes

Reaction equation

HRID 1696208 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

HCID 83823767HCID 83823767, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-48d8f1b2730f496891bef545b99a27f6
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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