Aluminium lithium hydride → HCID 67583567, compound

HRID 1456561Notes

Reaction equation

HRID 1456561 reaction equation
C(O[C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:33][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][C:18]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14][C@@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][N:8]2[CH3:6])[CH:31]=[CH:30][C:29]=1[F:32]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67583568HCID 67583568, compound

Product 1

HCID 67583567HCID 67583567, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

280 mg of (2R,4R)-1-t-butoxycarbonyl-2-[2-{2-[2-(3,4-difluorophenyl)-ethyl]-4-fluorophenoxy}ethyl]-4-hydroxypyrrolidine [prepared as described in step (b) above], 5 ml of tetrahydrofuran and 50 mg of lithium aluminum hydride were allowed to react together and subsequently treated in the same manner as described in step (b) of Example 1. The concentrated substance thus obtained was purified by silica gel column chromatography, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 140 mg (yield 63%) of the title compound as a colorless solid substance.

Workup

  1. customto react together
  2. additionsubsequently treated in the same manner
  3. customThe concentrated substance thus obtained
  4. customwas purified by silica gel column chromatography
  5. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-9cf219488793428985ea3de326d580fd
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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