Triethylamine → 1-Methylethyl 4-{(1R)-1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate

HRID 423658Notes

Reaction equation

HRID 423658 reaction equation
[OH:1][C@@H:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].[CH3:16][S:17](Cl)(=[O:19])=[O:18].CCN(CC)CC>C(Cl)Cl>[CH3:16][S:17]([O:1][C@@H:2]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)[CH3:3])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 666733431-methylethyl 4-[(1R)-1-hydroxyethyl]-1-piperidinecarboxylate

Product 1

HCID 866387501-Methylethyl 4-{(1R)-1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylateYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylethyl 4-{(1R)-1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate (0.7 g, 100%) was prepared as a light yellow oil from 1-methylethyl 4-[(1R)-1-hydroxyethyl]-1-piperidinecarboxylate (0.5 g, 2.32 mmol), methanesulfonyl chloride (0.22 mL, 2.79 mmol), Et3N (0.49 mL, 3.48 mmol) and CH2Cl2 (30 mL) in a manner similar to Example 150, Step 1. The crude material was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.88 (septet, 1H, J=6.2 Hz), 4.70-4.55 (m, 1H), 4.30-4.10 (m, 2H), 2.99 (s, 3H), 2.75-2.60 (m, 2H), 1.80-1.60 (m, 3H), 1.38 (d, 3H, J=6.3 Hz), 1.35-1.15 (m, 8H).

Workup

  1. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-99d8b4a7329443aea88353cedcd6ce68
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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