Sodium Bicarbonate → HCID 56983775, compound

HRID 1351858Notes

Reaction equation

HRID 1351858 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:16][C@H:17]([O:26][Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][C:9]=2[CH:41]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.C(=O)(O)[O-].[Na+]>O1CCCC1.CCCCCC>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:16][C@H:17]([O:26][Si:27]([CH2:28][CH3:29])([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][C:9]=2[CH:41]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21225700DiisobutylaluminumhydrideHCID 57302955HCID 57302955, compound

Product 1

HCID 56983775HCID 56983775, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a cold (−78° C.) solution of 8-[N-tert-butoxycarbonyl-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid methyl ester (5.90 g) in tetrahydrofuran (120 ml) was added dropwise a solution of diisobutylaluminum hydride in hexane (0.95M, 53.2 ml). The reaction mixture was warmed to room temperature over 4 hours, and then saturated sodium bicarbonate solution was added dropwise to the mixture. The resulting precipitate was filtered off and washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1) to afford N-(3-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxy-carbonylamine (5.20 g).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with ethyl acetate
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-909f49e40a734e229d74532cc40190aa
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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