Triethylamine → 4-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

HRID 423641Notes

Reaction equation

HRID 423641 reaction equation
[OH:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].[CH3:17][S:18](Cl)(=[O:20])=[O:19].CCN(CC)CC>>[CH3:17][S:18]([O:1][CH:2]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]1)[CH3:3])(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 232828864-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl esterYield 98.7%

Procedure

(±)-1,1-Dimethylethyl 4-{1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate (0.74 g, 49%) was prepared as a light brown oil from (±)-1,1-dimethylethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (0.56 g, 2.44 mmol), methanesulfonyl chloride (0.23 mL, 2.93 mmol) and Et3N (0.69 mL, 4.88 mmol) in a manner similar to Example 150, Step 1. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.70-4.55 (m, 1H), 4.20-4.10 (m, 2H), 2.99 (s, 3H), 2.70-2.55 (m, 2H), 1.80-1.60 (m, 3H), 1.43 (s, 9H), 1.38 (d, 3H, J=6.4 Hz), 1.35-1.15 (m, 2H).

Workup

  1. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-f13b9028dd1b4da4b88380c1d21493be
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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