Valeryl chloride → HCID 67100005, compound

HRID 2166992Notes

Reaction equation

[F:1][CH:2]([F:17])[C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([OH:10])[CH2:6][N:5](C(=O)CCCC)[CH2:4]1.C([Cl:24])(=O)CCCC>>[ClH:24].[F:17][CH:2]([F:1])[C@H:3]1[CH2:4][NH:5][CH2:6][C@@H:7]([OH:10])[C@@H:8]1[OH:9]

Participants

Reactant 2

HCID 61186Valeryl chloride

HCID 51356754HCID 51356754, compound

Product 1

HCID 67100005HCID 67100005, compound

Procedure

1-((3S,4R,5R)-3-(Difluoromethyl)-4,5-dihydroxypiperidine-1-yl)pentane-1-one (8a; Z=CO; R5=butyl). Following General Procedure D, except that the reaction was run at room temperature and using pentanoyl chloride (0.17 g, 1.4 mmol), the title compound was obtained as a white solid (0.26 g, 71%). MH+=252. 1H NMR (DMSO-d6) 5.9-6.5 (dt, 1H), 5.35 (m, 1H, ex), 5.25 (m, 1H), ex), 4.2 (dd, 1H), 3.75 (dd, 1H), 3.35 (m, 2H), 3.1 (m, 1H), 2.85 (m, 1H), 2.3 (t, 2H), 1.9 br m, 1H), 1.4 (m, 2H), 1.25 (m, 2H), 0.85 (t, 3H).

Workup

customwas run at room temperature

Sources & evidence

ORD record: ord-440d6f0278c448e79e0aa37285902795
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09044437B2

Reaction notes

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