Triethylamine → HCID 86606911, compound

HRID 747000Notes

Reaction equation

HRID 747000 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:46])([F:45])[C:17]1[CH:18]=[C:19]([C@H:27]([O:29][C@@H:30]2[C@@H:35]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[C@H:34]([CH:43]=O)[CH2:33][CH2:32][O:31]2)[CH3:28])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.FC(F)(F)C(O)=O.[CH2:54]1[C:58]2([CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[C@@H:57]([O:64][C:65]([C@@:67]23[C:73]([CH3:75])([CH3:74])[C@@:70]([CH3:76])([CH2:71][CH2:72]2)[C:69](=[O:77])[O:68]3)=[O:66])[CH2:56][O:55]1.C(N(CC)CC)C>ClCCl>[F:46][C:16]([F:15])([F:45])[C:17]1[CH:18]=[C:19]([C@H:27]([O:29][C@@H:30]2[C@@H:35]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[C@H:34]([CH2:43][N:61]3[CH2:62][CH2:63][C:58]4([CH2:54][O:55][CH2:56][C@@H:57]4[O:64][C:65]([C@@:67]45[C:73]([CH3:74])([CH3:75])[C@@:70]([CH3:76])([CH2:71][CH2:72]4)[C:69](=[O:77])[O:68]5)=[O:66])[CH2:59][CH2:60]3)[CH2:33][CH2:32][O:31]2)[CH3:28])[CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86601740(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)-tetrahydropyran-4-carbaldehydeHCID 86606912HCID 86606912, compound

Product 1

HCID 86606911HCID 86606911, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid sodium triacetoxyborohydride (107 mg, 0.504 mmol) was added to a stirred mixture of 2-[1-{(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)-tetrahydropyran-4-carbaldehyde (Description 11; 121 mg, 0.36 mmol), (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (4R)-2-oxa-8-aza-spiro[4.5]dec-4-yl ester trifluoroacetate (Description 10; 130 mg), triethylamine (0.1 ml, 0.72 mmol) and dichloromethane (3 ml) at room temperature. The mixture was stirred for 45 minutes, quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The organic extract was dried (Na2SO4) and concentrated. The residue was purified by preparative TLC (dichloromethane:methanol) to give the title compound (100 mg). The HCl salt was prepared and recrystallised from ethyl acetate:methanol.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (dichloromethane:methanol)

Sources & evidence

ORD record
ord-586e6d7867a8475cbee1cb0867d77a31
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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