Methyl chloroformate → (S)-(1-{4-[4-(4-Ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-carbamic acid methyl ester

HRID 1617327Notes

Reaction equation

HRID 1617327 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:3].CCN(C(C)C)C(C)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C1COCC1>[CH3:39][O:38][C:36](=[O:37])[NH:25][C@H:23]([C:20]1[CH:19]=[CH:18][C:17]([N:14]2[CH2:13][CH2:12][CH:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:2][CH3:3])=[CH:10][CH:9]=3)[CH2:16][CH2:15]2)=[CH:22][CH:21]=1)[CH3:24]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86688559(S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride

Product 1

HCID 86688561(S)-(1-{4-[4-(4-Ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 36.1 mg (0.10 mmol) (S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride (XII.1) and 42.7 μL (0.250 mmol) DIPEA in 2 mL THF are added 11.64 (0.150 mmol) methyl chloroformate at 0° C. The mixture is stirred for 12 h at rt. The solvent is removed under reduced pressure, the residue is taken up in DMF and purified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol) to yield the desired product.

Workup

  1. customThe solvent is removed under reduced pressure
  2. custompurified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol)

Sources & evidence

ORD record
ord-292a4892b26744768d36e9fff485f352
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

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