Water → ethyl (R)-quinuclidin-3-yl carbonate

HRID 1171851Notes

Reaction equation

C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([OH:22])[CH2:15]2.O>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:9](=[O:10])([O:22][C@@H:16]1[CH:17]2[CH2:20][CH2:21][N:14]([CH2:19][CH2:18]2)[CH2:15]1)[O:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: 20 °C

Procedure

In 100 ml of chloroform and in the presence of 16 g of triethylamine and 0.1 g of 4-dimethylaminopyridine, 12.8 g of ethyl chloroformate was added to 10.0 g of (R)-quinuclidin-3-ol at 10° C. This was heated to 20° C., stirred for 2 hours and mixed with 50 ml of water, the thus obtained organic layer was washed with 50 ml of water, and then the organic layer was concentrated under a reduced pressure and dried in vacuo to obtain 15.49 g of a oily substance. By purifying this oily substance by a silica gel column chromatography, 7.24 g of ethyl (R)-quinuclidin-3-yl carbonate was obtained (1H-NMR (DMSO-d6, tetramethylsilane internal standard): δ 1.21 (3H, t, J=7.2 Hz), 1.26-1.37 (1H, m), 1.42-1.53 (1H, m), 1.55-1.70 (2H, m), 1.91-1.98 (1H, m), 2.48-2.76 (5H, m), 3.06-3.17 (1H, m), 4.11 (2H, q, J=7.2 Hz), 4.56-4.64 (1H, m), mass spectrum: m/z=200 [M+H]+ (FAB)).

Workup

washthe thus obtained organic layer was washed with 50 ml of water
concentrationthe organic layer was concentrated under a reduced pressure
customdried in vacuo
customto obtain 15.49 g of a oily substance
customBy purifying this oily substance by a silica gel column chromatography

Sources & evidence

ORD record: ord-ea97c7ca817d4462989b44926856270c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829715B2

Reaction notes

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