Hydrochloric Acid → (S)-1-amino-2-methyl-1-phenylpropan-2-ol

HRID 588113Notes

Reaction equation

HRID 588113 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:12])([CH3:11])[CH3:10])(C)(C)C.O1CCOCC1.Cl>C(Cl)Cl>[NH2:7][C@@H:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([CH3:11])([OH:12])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58291964(S)-tert-butyl(2-hydroxy-2-methyl-1-phenylpropyl)carbamate

Product 1

HCID 46941324(S)-1-amino-2-methyl-1-phenylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl(2-hydroxy-2-methyl-1-phenylpropyl)carbamate (3.5 g, 13 mmol) in CH2Cl2 (20 mL) was added dioxane saturated with HCl gas (10 mL) and the contents were stirred at ambient temperature for 30 min. The volatiles were then removed under reduced pressure and the residue thus obtained was triturated with Et2O to afford (S)-1-amino-2-methyl-1-phenylpropan-2-ol. 1H NMR (300 MHz, DMSO-d6) δ 8.3 (bs, 2H), 7.47-7.37 (m, 5H), 5.34 (s, 1H), 4.1 (bs, 1H), 1.17 (s, 3H), 0.97 (s, 3H). Anal. Calcd. C10H15NO 165.2. Found 166.2 (M+H).

Workup

  1. customThe volatiles were then removed under reduced pressure
  2. customthe residue thus obtained
  3. customwas triturated with Et2O

Sources & evidence

ORD record
ord-98dd9a63cb5f462799dbed254ccde52c
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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