Aluminium lithium hydride → HCID 54563963, compound

HRID 1456557Notes

Reaction equation

HRID 1456557 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][CH:29]=[CH:28][CH:27]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][C@@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][N:8]2[CH3:6])=[C:18]([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54502309HCID 54502309, compound

Product 1

HCID 54563963HCID 54563963, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1115 mg of (2R,4R)-1-t-butoxycarbonyl-2-{2-[4-fluoro-2-(2-phenylethyl)-phenoxy]ethyl}-4-hydroxypyrrolidine [prepared as described in step (a) above], 20 ml of tetrahydrofuran and 200 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 5:1 by volume mixture of methylene chloride and methanol as the eluent, to give 540 mg (yield 61%) 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-9836243c3e26414583d9fe252f455d85
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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