Hydrochloric Acid → (2R,3R)-3-Amino-2-methyl-3-phenylpropan-1-ol

HRID 1697420Notes

Reaction equation

HRID 1697420 reaction equation
[Si]([O:18][CH2:19][C@H:20]([CH3:35])[C@@H:21]([NH:28]S(C(C)(C)C)=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>CO>[NH2:28][C@@H:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:20]([CH3:35])[CH2:19][OH:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66688903N-[(1R,2R)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1-phenylpropyl]-2-methylpropane-2-sulfinamide

Product 1

HCID 12452700(2R,3R)-3-Amino-2-methyl-3-phenylpropan-1-olYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

N-[(1R,2R)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1-phenylpropyl]-2-methylpropane-2-sulfinamide (Example 136b, 1.46 g) was stirred in methanol (10 mL) and then Hydrogen chloride (4M in dioxane) (10 mL) added. The reaction was stirred at 70° C. for 7 h and then concentrated in vacuo. The crude product was azeotroped with toluene then triturated in ether for 2 days after which the solvent was concentrated in vacuo to give the subtitle compound (0.47 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was azeotroped with toluene
  3. customthen triturated in ether for 2 days after which the solvent
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-943dba765ba341d1822892f021ff2ef8
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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