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

HRID 337162Notes

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-005f8068162e489bb50fe8bf039ab519
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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