Water → (3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one

HRID 1267838Notes

Reaction equation

C(OC([NH:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][NH:11][C:10]1=[O:24])=O)(C)(C)C.C[Si](I)(C)C.O>C(Cl)Cl.CO>[NH2:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:19])[CH2:12][NH:11][C:10]1=[O:24]

Participants

Conditions

Temperature: -78 °C

Procedure

(3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-tert-butyidimethylsilyloxy-2H-azepin-2-one (8.0 g, 22 mmol) is dissolved in 40 mL of CH2Cl2 and cooled to −78° C. Trimethylsilyl iodide (3.5 mL, 24.5 mmol) is added slowly. The mixture is allowed to react at −78° C. for 30 min. The reaction is warmed to 0° C. and stirred for 15 min. The solution turned yellow. The reaction is quenched with NH4HCO3 (3.43 g, 44 mmol) dissolved in 30 mL of CH3OH, and 15 mL water. The mixture is concentrated and chromatographed with 95:5 mixture of CH2Cl2 and methanol to yield 5.45 g (96%) of (3S, 6R)-3-aminohexahydro-6-tert-butyl-dimethylsilyloxy-2H-azepin-2-one as a white solid: 1H NMR (CDCl3) δ 5.61 (s, 1H), 3.88 (s, 1H), 3.42 (d, J=8 Hz, 1H), 3.32 (dd, J=6 Hz and 16 Hz, 1H), 3.06 (m, 1H), 1.87 (m, 2H), 1.76 (m, 1H), 1.65 (s, 3H), 0.83 (s, 9H), 0.001 (s, 6H).

Workup

customto react at −78° C. for 30 min
temperatureThe reaction is warmed to 0° C.
concentrationThe mixture is concentrated
customchromatographed with 95:5 mixture of CH2Cl2 and methanol

Sources & evidence

ORD record: ord-25e0ecd776914dc890f2379815ab1f74
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555533B2

Reaction notes

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