Aluminium lithium hydride → HCID 67266649, compound

HRID 602815Notes

Reaction equation

HRID 602815 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH2:12][C:13]2[N:17]=[C:16]([C:18]([S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])([CH:20]3[CH2:32][C:23]4[NH:24][C:25]5[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][C:30]=5[C:22]=4[CH2:21]3)[F:19])[O:15][N:14]=2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:36]1([S:33]([C:18]([CH:20]2[CH2:32][C:23]3[NH:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][C:30]=4[C:22]=3[CH2:21]2)([F:19])[C:16]2[O:15][N:14]=[C:13]([CH2:12][NH:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=3)[N:17]=2)(=[O:35])=[O:34])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67011601HCID 67011601, compound

Product 1

HCID 67266649HCID 67266649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 27 mg (0.04 mmol) of (RS,SR)-4-[({5-[-benzenesulfonyl-(-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-amino)-methyl]-benzoic acid methyl ester (example 129.3) in 2 mL THF at 0° C., 40 μl (0.04 mmol, 1 eq) lithium aluminum hydride (1M solution in THF) were added. The reaction mixture was stirred at 0° C. for 1 hour and then at RT for 30 minutes. The reaction was quenched with a saturated NaHCO3 aqueous solution, and the crude product extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (heptane/EtOAc 2:8) yielded 12 mg (48%) of (RS,SR)-{4-[{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-amino)-methyl]-phenyl}-methanol as a light yellow powder, MS: 581 (MH+).

Workup

  1. waitat RT for 30 minutes
  2. customThe reaction was quenched with a saturated NaHCO3 aqueous solution
  3. extractionthe crude product extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customColumn chromatography on silica gel (heptane/EtOAc 2:8) yielded 12 mg (48%) of (RS,SR)-{4-[{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-amino)-methyl]-phenyl}-methanol as a light yellow powder, MS

Sources & evidence

ORD record
ord-ad525961aad44f30ade9f8a29ea3e3a7
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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