Potassium bis(trimethylsilyl)amide → benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(prop-1-en-2-yl)cyclohexylcarbamate

HRID 1374300Notes

Reaction equation

[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([C@@H:14]1[CH2:19][C@H:18]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:17][CH2:16][C@@H:15]1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Si:21]([O:20][C@@H:18]1[CH2:17][CH2:16][C@H:15]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@H:14]([C:11]([CH3:12])=[CH2:1])[CH2:19]1)([C:24]([CH3:25])([CH3:27])[CH3:26])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyltriphenylphosphonium bromide (1.2 g) was suspended in toluene (16 mL) prior to the addition of 0.5M potassium bis(trimethylsilyl)amide (5.8 mL) in toluene. After 1 h, this solution was cooled to 0° C. prior to the addition of benzyl (1S,2R,4R)-2-acetyl-4-(tert-butyldimethylsilyloxy)cyclohexylcarbamate (660 mg) in toluene (5.4 mL). After 20 min at 0° C., the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (2×). The organic extracts were combined, washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by flash chromatography to afford benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(prop-1-en-2-yl)cyclohexylcarbamate (380 mg). MS found: (M+H)+=404.2.

Workup

waitAfter 20 min at 0° C.
customthe reaction was quenched with saturated NH4Cl solution
extractionextracted with EtOAc (2×)
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record: ord-db4fd3c49bfa47b780cde2eb93c3be4e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163937B2

Reaction notes

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