Benzaldehyde → HCID 67346582, compound

HRID 1669436Notes

Reaction equation

HRID 1669436 reaction equation
[NH2:1][C@@H:2]1[CH2:9][N:8]2[C:10]3[CH:11]=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:13]=[CH:14][C:15]=3[C:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:7]2[C:6]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:5]=2[O:4][CH2:3]1.C(OC)(OC)OC.[CH:39](=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[BH3-]C#N.[Na+]>>[CH2:39]([NH:1][C@@H:2]1[CH2:9][N:8]2[C:10]3[CH:11]=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:13]=[CH:14][C:15]=3[C:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:7]2[C:6]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:5]=2[O:4][CH2:3]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 9005Trimethyl orthoformate2×HCID 5003444Sodium cyanoborohydrideHCID 67345381HCID 67345381, compound

Product 1

HCID 67346582HCID 67346582, compound

Procedure

Methyl (7R)-7-amino-14-cyclohexyl-3-fluoro-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (Example 11, Step 5) was dissolved in HC(OMe)3 (50 eq) and a solution of benzaldehyde (1.1 eq) in HC(OMe)3 (50 eq) was added. The mixture was stirred overnight at RT to allow formation of the imine. All volatiles were evaporated and the residual material was dissolved in MeOH/HOAc (0.05 M). NaCNBH3 (1.1 eq) was added and the mixture was stirred at RT for 1 h. The solution was used directly in the next step. (ES+) m/z 513 (M+H)+.

Workup

  1. customAll volatiles were evaporated
  2. dissolutionthe residual material was dissolved in MeOH/HOAc (0.05 M)
  3. stirringthe mixture was stirred at RT for 1 h

Sources & evidence

ORD record
ord-4d9fe03541144a6bab92d9b866e07735
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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