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

HRID 2070842Notes

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

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

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

Sources & evidence

ORD record: ord-d1ef85c4437a41ecb83ea0770d2901c6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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