Trifluoroacetic acid → 3-Amino-1-methylcyclohexan-1-ol

HRID 1749504Notes

Reaction equation

HRID 1749504 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8]C(=O)OC(C)(C)C)[CH2:3]1.[C:16](O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:16])([OH:1])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21925254tert-Butyl (3-hydroxycyclohexyl)carbamate

Product 1

HCID 134950983-Amino-1-methylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude tert-butyl (3-hydroxycyclohexyl)carbamate (4.0 g, crude) in DCM (40 mL) was added TFA (20 mL) under cooling in an ice bath. The resulting reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated to give a crude product (3.0 g, crude), which was used in the next step without further purification. MS (ESI) m/z 130.1 [M+H]+.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThe resulting reaction mixture
  3. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4dbb77d86cb94a1f916a1ed0a16741c6
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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