Sodium Carbonate → HCID 57224461, compound

HRID 1838732Notes

Reaction equation

HRID 1838732 reaction equation
O[C@@H](C1C=CC=CC=1)C([O:5][C@@H:6]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@H:10]([CH2:20][O:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][N:8]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:7]1)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[CH2:41]([N:8]1[CH2:9][C@@H:10]([CH2:20][O:21][C:22]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:6]([OH:5])[CH2:7]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 57123125HCID 57123125, compound

Product 1

HCID 57224461HCID 57224461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

33.3 (46.13 mmol) of (3R,4R,5S)-1-benzyl-4-(4-methoxy-phenyl)-5-trityloxymethyl-piperidin-3-ol (S)-hydroxy-phenyl-acetate were treated with a cold aqueous solution of 7.3 g (69.2 mmol) of sodium carbonate in 100 ml water and 600 ml of ethyl acetate. The aqueous phase was separated and extracted twice with 200 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated under reduced pressure to yield 25 g of (3R,4R,5S)-1-benzyl-4-(4-methoxy-phenyl)-5-trityloxymethyl-piperidin-3-ol as a colorless oil which was directly used without further purification.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted twice with 200 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2141b88e84e740b888401ba08131bce1
Source dataset
uspto-grants-2004_01
Patent number
US06673931B2

Reaction notes

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