Triethylamine → Cis(+/-)2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethyl methanesulfonate

HRID 255335Notes

Reaction equation

HRID 255335 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH2:11][C@H:10]1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.CS(OCCN1CCC(NC(OC(C)(C)C)=O)CC1)(=O)=O>>[CH3:27][S:28]([O:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][C@H:9]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:10]([O:18][CH3:19])[CH2:11]1)(=[O:30])=[O:29]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonateHCID 602017752-[(3R,4S)-4-(Dibenzylamino)-3-methoxypiperidin-1-yl]ethanol2×

Product 1

HCID 86642652Cis(+/-)2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethyl methanesulfonate

Procedure

Cis(±)2-[4-(dibenzylamino)-3-methoxypiperidin-1-yl]ethanol (Intermediate 170, 740 mg, 2.1 mmol) was reacted with methanesulfonyl chloride (0.20 mL, 2.5 mmol) in the presence of triethylamine (0.41 mL, 2.9 mmol) as described for Intermediate 6. The crude product was presumed to be unstable and was used without further purification directly for the next step.

Workup

  1. customwas used without further purification directly for the next step

Sources & evidence

ORD record
ord-468b698ae07d44469d91b90c7f81bb0b
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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