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

HRID 1644463Notes

Reaction equation

HRID 1644463 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-ee7abde29831440288bb8186720bdb6f
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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