HCID 69544084, compound → HCID 22242907, compound

HRID 891669Notes

Reaction equation

HRID 891669 reaction equation
C(OC(=O)[NH:10][CH:11]([CH2:31][O:32][Si:33]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1>CO.[Pd]>[Si:14]([O:13][CH2:12][CH:11]([NH2:10])[CH2:31][O:32][Si:33]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:27]([CH3:28])([CH3:29])[CH3:30])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 69544084HCID 69544084, compound

Product 1

HCID 22242907HCID 22242907, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [2-(t-butyldiphenylsilyloxy)-1-(t-butyldiphenylsilyloxymethyl)ethyl]carbamic acid benzyl ester (13.6 g, 19.5 mmol) (obtained as described in Reference Example 39(2)) in methanol (410 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (13.6 g) at room temperature for 3.5 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:methanol (98:2→9:1) as the eluant to afford 2-(t-butyldiphenylsilyloxy)-1-(t-butyldiphenylsilyloxymethyl)ethylamine (9.34 g, yield 84%) as a colorless oil.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f5d7bf2d1ef54249ae3253c81ddda090
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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