Hydrochloric Acid → N-BOC-(3-hydroxy-5,7-dimethyladamant-1-yl)-glycine

HRID 890233

Reaction equation

[C:1]([N:8]([C:13]12[CH2:22][C:17]3([CH3:23])[CH2:18][CH:19]([CH2:21][C:15]([CH3:24])([CH2:16]3)[CH2:14]1)[CH2:20]2)[CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O-:25][Mn](=O)(=O)=O.[K+].Cl>[OH-].[K+].O.CCOC(C)=O>[C:1]([N:8]([C:13]12[CH2:14][C:15]3([CH3:24])[CH2:16][C:17]([CH3:23])([CH2:18][C:19]([OH:25])([CH2:21]3)[CH2:20]1)[CH2:22]2)[CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-BOC-(3,5-dimethyladamantan-1-yl)-glycine (1.79 g, 5.3 mmol) in 2% KOH/water (75 mL) at rt was added KMnO4 (1.0 g, 6.3 mmol). The reaction was heated to 90° C. for 2 h. An additional portion of KMnO4 (0.3 g, 1.9 mmol) was added and the reaction was heated at 90° C. for an additional 1.5 h. The reaction was then diluted with EtOAc (150 mL) and with vigorous mixing the pH was addjusted to ˜3 with 1N HCl. The EtOAc layer was separated and set aside. The aqueous layer was then extracted once more with EtOAc and twice with dichloromethane. The combined organics were dried over MgSO4, filtered and concentrated to give N-BOC-(3-hydroxy-5,7-dimethyladamant-1-yl)-glycine (1.91 g). MS m/e (M+H)+=354.2

Workup

temperaturethe reaction was heated at 90° C. for an additional 1.5 h
additionwith vigorous mixing the pH
customThe EtOAc layer was separated
extractionThe aqueous layer was then extracted once more with EtOAc and twice with dichloromethane
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-048587230b6b4becab8d8bc15da7682b
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995183B2

Linked notes

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