Methanol → HCID 69433111, compound

HRID 1295359Notes

Reaction equation

HRID 1295359 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[C@@:10]([CH2:14][NH2:15])([CH2:11]2)[C@@H:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([N:28]([CH3:36])[C:29](=[O:35])[C@@H:30]3[CH2:34][C@@H:31]32)=[CH:26][C:25]=1[CH:37]=O.CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[C@@:10]([CH2:14][NH:15][CH2:37][C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][C:24]=3[O:23][CH3:22])[C@H:31]3[CH2:34][C@H:30]3[C:29](=[O:35])[N:28]4[CH3:36])([CH2:11]2)[C@@H:9]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 69335700HCID 69335700, compoundHCID 86602044HCID 86602044, compound

Product 1

HCID 69433111HCID 69433111, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Racemic Intermediate 21, one enantiomer being (1R,2S,5S)-1-aminomethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.055 g, 0.19 mmol) was combined with (1aR,7bS)-6-methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde (0.046 g, 0.20 mmol) in methylene chloride (3 mL) and the mixture was stirred for 3.0 hours. APCI mass spec showed complete imine formation (m+1: 503). Methanol (1.0 mL) and sodium triacetoxyborohydride (0.053 g, 0.25 mmol) were added and the reaction allowed to stir for 16 hours. The solvent was removed at reduced pressure and the residue was partitioned between saturated sodium bicarbonate solution and methylene chloride, the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as a white foam (0.10 g, quantitative crude yield). This material was used without further purification.

Workup

  1. stirringto stir for 16 hours
  2. customThe solvent was removed at reduced pressure
  3. customthe residue was partitioned between saturated sodium bicarbonate solution and methylene chloride
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-721a349ff25c42d0ab368ce1170cec7f
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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