Hydrochloric Acid → HCID 58380917, compound

HRID 38449Notes

Reaction equation

HRID 38449 reaction equation
C([Si](C)(C)[O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([C:10]3([NH:23]S(C(C)(C)C)=O)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]1)[CH2:14]2)(C)(C)C.Cl>CC(O)C>[C:17]1([C:10]2([NH2:23])[CH:11]3[CH2:16][C:7]4([OH:6])[CH2:14][CH:13]([CH2:15][CH:9]2[CH2:8]4)[CH2:12]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 583809012-Methyl-propane-2-sulfinic acid [5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-adamantan-2-yl]-amide

Product 1

HCID 58380917HCID 58380917, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid [5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-adamantan-2-yl]-amide (6) in 2-propanol (10 mL) was added 1N hydrochloric acid (5 mL) and the mixture was stirred at room temperature until complete conversion was achieved. The reaction mixture was washed with diethyl ether, the aqueous phase was concentrated in vacuo and lyophilized to yield 676 mg of a diastereomeric mixture of 4-phenyl-4-amino-adamantan-1-ol (7) as its hydrochloride. Rt=0.33 min, 0.85 min (Method 3). Detected mass: 227.2 (M-NH3+H+).

Workup

  1. washThe reaction mixture was washed with diethyl ether
  2. concentrationthe aqueous phase was concentrated in vacuo

Sources & evidence

ORD record
ord-3a0642bf72854cb7aba3a5fae477ee9c
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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