Triethylamine → HCID 86638743, compound

HRID 423598Notes

Reaction equation

[OH:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)[CH3:3].CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:1][CH:2]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:8][CH2:9]1)[CH3:3])(=[O:30])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (±)-phenylmethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (0.64 g, 2.43 mmol), Et3N (1.03 mL, 7.29 mmol) in CH2Cl2 (50 mL) at 0° C. was treated dropwise with methanesulfonyl chloride (0.38 mL, 4.86 mmol). The reaction mixture was stirred at 0° C. for 1 h, then at ambient temperature for 1.5 h, diluted with CH2Cl2 (100 mL) and washed with 1M NaH2PO4 (50 mL×2) and brine (25 mL). The CH2Cl2 layer was dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light brown oil. The crude product was purified by flash chromatography on an ISCO silica gel column using 0 to 45% EtOAc/hexanes to give 0.73 g (88%) of (±)-phenylmethyl 4-{1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.40-7.25 (m, 5H), 5.12 (s, 2H), 4.70-4.60 (m, 1H), 4.25 (bs, 2H), 2.99 (s, 3H), 2.80-2.65 (m, 2H), 1.85-1.60 (m, 3H), 1.40 (d, 3H, J=6.4 Hz), 1.35-1.20 (m, 2H).

Workup

waitat ambient temperature for 1.5 h
washwashed with 1M NaH2PO4 (50 mL×2) and brine (25 mL)
dry with materialThe CH2Cl2 layer was dried over Na2SO4
filtrationfiltered
concentrationthe filtrate was concentrated
customto give the crude product as a light brown oil
customThe crude product was purified by flash chromatography on an ISCO silica gel column

Sources & evidence

ORD record: ord-8184763430a646609d07d532a935119f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101634B2

Reaction notes

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