Sodium borohydride → tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

HRID 530867Notes

Reaction equation

HRID 530867 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](OC)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO.C(Cl)Cl>[OH:16][CH2:15][CH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59453914Methyl 3-(tert-butoxycarbonylamino)cyclohexanecarboxylate

Product 1

HCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

Reagents, catalysts & solvents 1

HCID 22912779methanol THF dichloromethaneSolvent

Procedure

To a solution of methyl 3-(tert-butoxycarbonylamino)cyclohexanecarboxylate (9 mmol) in THF/MeOH/CH2Cl2 (36 ml, 10:1:1) was added NaBH4 (22.5 mmol) and stirred at rt overnight. The reaction was quenched with water and extracted with CH2Cl2 (3×10 mL). The extracts were combined and dried using anhydrous sodium sulfate. The product was purified using Biotage.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. customdried
  4. customThe product was purified

Sources & evidence

ORD record
ord-a5507b277d9543b8a7e79c784e16ef3d
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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