Water → HCID 53654596, compound

HRID 1375014Notes

Reaction equation

HRID 1375014 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([OH:22])[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Si:30](Cl)([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][Si:30]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 54425425HCID 54425425, compound

Product 1

HCID 53654596HCID 53654596, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-1-tert-butoxycarbonyl-2-(3-hydroxy-4-methylbenzyl)piperazine (7.73 g) and 4-dimethylaminopyridine (620 mg) in dichloromethane (90 ml) was added successively triethylamine (15.82 ml) and tert-butyldiphenylsilyl chloride (26.24 ml) at room temperature. After stirring under reflux for 27.5 hours, water (200 ml) was added to the mixture, and the mixture was extracted with dichloromethane (100 ml, 50 ml×2). The combined organic extracts were washed successively with water and brine, dried over magnesium sulfate, and evaporated under reduced pressure to give crude oil. The oil was purified with column chromatography (silica gel, 500 ml, methanol:dichloromethane 5:95) to give (2R)-1-tert-butoxycarbonyl-2-(3-tert-butyldiphenylsilyloxy-4-methylbenzyl)piperazine (12.07 g) as a solid.

Workup

  1. temperatureunder reflux for 27.5 hours
  2. extractionthe mixture was extracted with dichloromethane (100 ml, 50 ml×2)
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto give crude oil
  7. customThe oil was purified with column chromatography (silica gel, 500 ml, methanol:dichloromethane 5:95)

Sources & evidence

ORD record
ord-f44298efe19c4909ab8ded6662065d31
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

Loading…