Diisobutylaluminumhydride → HCID 86606927, compound

HRID 747030Notes

Reaction equation

HRID 747030 reaction equation
[F:1][C:2]([F:55])([F:54])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C@H:20]([CH2:29][N:30]3[CH2:53][CH2:52][C:33]4([CH2:37][O:36][CH2:35][CH:34]4[O:38]C([C@@]45C(C)(C)[C@@](C)(CC4)C(=O)O5)=O)[CH2:32][CH2:31]3)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[F:55][C:2]([F:1])([F:54])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C@H:20]([CH2:29][N:30]3[CH2:53][CH2:52][C:33]4([CH2:37][O:36][CH2:35][C@H:34]4[OH:38])[CH2:32][CH2:31]3)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86760700HCID 86760700, compound

Product 1

HCID 86606927HCID 86606927, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4RS)-8-{(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)-tetrahydropyran-4-ylmethyl}-2-oxa-8-aza-spiro[4.5]dec-4-yl ester (Description 12; 138 mg, 0.175 mmol) in dichloromethane (5 ml) was cooled to −78° C. and diisobutylaluminium hydride (1.5M in toluene, 0.5 ml, 0.75 mmol) added. The reaction was stirred for 30 minutes then quenched by the addition of 2M aqueous sodium hydroxide solution. The mixture was allowed to warm to room temperature then dried over Na2SO4 and filtered through Celite™. The filtrate was concentrated in vacuo and the residue purified by preparative thin layer chromatography, eluting with 7% methanol/dichloromethane to give the title compound (27 mg, 26%).

Workup

  1. customthen quenched by the addition of 2M aqueous sodium hydroxide solution
  2. dry with materialthen dried over Na2SO4
  3. filtrationfiltered through Celite™
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by preparative thin layer chromatography
  6. washeluting with 7% methanol/dichloromethane

Sources & evidence

ORD record
ord-3f57b192c5884a8492ab9cec7ad5c700
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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