Hydrogen Bromide → (+/-)-(1S,2S)-2-amino-1-methylcyclohexanolhydrobromide

HRID 1408956Notes

Reaction equation

HRID 1408956 reaction equation
[OH:1][C@@:2]1([CH3:19])[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8]C(=O)OCC1C=CC=CC=1.[BrH:20]>CC(O)=O>[BrH:20].[NH2:8][C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@:2]1([CH3:19])[OH:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86707706(+/-)-benzyl (1S,2S)-2-hydroxy-2-methylcyclohexylcarbamate

Product 1

HCID 86707707(+/-)-(1S,2S)-2-amino-1-methylcyclohexanolhydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To (±)-Benzyl (1S,2S)-2-hydroxy-2-methylcyclohexylcarbamate (81.4 mg, 0.309 mmol) was added HBr in AcOH, 33% (1 mL, 6.1 mmol) and the resulting mixture was stirred at rt under N2 for 2 h. The solvents were removed and the crude residue concentrated with EtOH (2×) and dried on high vacuum overnight to afford an orange low-melting solid which was used directly in the next step.

Workup

  1. customThe solvents were removed
  2. concentrationthe crude residue concentrated with EtOH (2×)
  3. customdried on high vacuum overnight
  4. customto afford an orange low-melting solid which

Sources & evidence

ORD record
ord-7eaf93c4e5f042c0b3f0639cad8a2d94
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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