tert-Butyl methyl ether → HCID 66615617, compound

HRID 1878796Notes

Reaction equation

HRID 1878796 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[C:6]([CH3:38])=[C:7]([CH:34]=[CH:35][C:36]=1[Cl:37])[O:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C@@H:22]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23]([O:25]C)=[O:24])[CH2:18][CH2:17]2)[CH2:11][CH2:10]1.C([O-])(=O)C.[NH4+].C(OC)(C)(C)C>O.CO.C1COCC1>[Cl:4][C:5]1[C:6]([CH3:38])=[C:7]([CH:34]=[CH:35][C:36]=1[Cl:37])[O:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([C@@H:22]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23]([OH:25])=[O:24])[CH2:20][CH2:21]2)[CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 168937Lithium hydroxide, monohydrateHCID 517165Ammonium AcetateHCID 66615615HCID 66615615, compound

Product 1

HCID 66615617HCID 66615617, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (30.5 g) in water (180 mL) was added dropwise to an ice cooled solution of methyl (2S)-2-(4-{[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]methyl}piperidin-1-yl)-3-phenylpropanoate (from step A) in methanol (115 mL) and THF (450 mL). The mixture was stirred at room temperature overnight. A solution of ammonium acetate (165 g) in water (300 mL) was added to the reaction mixture, followed by tert-butylmethyl ether (300 mL). The two phase mixture was stirred rapidly for 2 h. The solid was collected, washed with water (3×300 mL) and diethyl ether (3×200 mL). The solid was added to diethyl ether and stirred for 1 h then filtered. Fresh diethyl ether was added and the stirring, filtering procedure was repeated. The solid obtained was dried under vacuum at 50° C. overnight to give the title compound (33 g).

Workup

  1. stirringThe two phase mixture was stirred rapidly for 2 h
  2. customThe solid was collected
  3. washwashed with water (3×300 mL) and diethyl ether (3×200 mL)
  4. additionThe solid was added to diethyl ether
  5. stirringstirred for 1 h
  6. filtrationthen filtered
  7. additionFresh diethyl ether was added
  8. filtrationthe stirring, filtering procedure
  9. customThe solid obtained
  10. customwas dried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-adda386eab8c43dd9c26e6b60a8aaf60
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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