Triethylamine → 2-{6-[(Tert-butoxycarbonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl)ethyl methanesulfonate

HRID 255255Notes

Reaction equation

HRID 255255 reaction equation
OCCN1CC2C(C2NC(=O)OC(C)(C)C)C1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:30][S:31]([O:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][CH:40]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:39][CH2:38]1)(=[O:33])=[O:32].S([O-])(=O)(=O)C>C(Cl)(Cl)Cl>[CH3:30][S:31]([O:34][CH2:35][CH2:36][N:37]1[CH2:38][CH:39]2[CH:41]([CH:40]2[NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:42]1)(=[O:32])=[O:33]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonateHCID 86642627Tert-butyl[3-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamate2×

Product 1

HCID 866426262-{6-[(Tert-butoxycarbonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of tert-butyl [3-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamate (Intermediate 96) (376 mg, 1.55 mmol) and triethyl amine (0.283 mL, 3 mmol) in anhydrous chloroform (15 mL) was added at 0° C. methanesulfonyl chloride (228 mg, 3 mmol) via syringe. The reaction was allowed to warm to room temperature over 1 hr and worked up as described for Intermediate 6. The crude mesylate was used for the next step without delay.

Sources & evidence

ORD record
ord-663477ace79c47caaaa8bcbfdfdf1eb3
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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