Formaldehyde → HCID 56660575, compound

HRID 1392997Notes

Reaction equation

HRID 1392997 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[CH:7]3[C:14]4([CH2:15][CH2:16][C:5]=2[CH:4]=1)[CH:10]([CH2:11][NH:12][CH2:13]4)[CH2:9][CH2:8]3.C=O.[BH3-][C:22]#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[CH:7]3[C:14]4([CH2:15][CH2:16][C:5]=2[CH:4]=1)[CH:10]([CH2:11][N:12]([CH3:22])[CH2:13]4)[CH2:9][CH2:8]3

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67424147HCID 67424147, compound2×

Product 1

HCID 56660575HCID 56660575, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methoxy-5,6,6a,7,8,9,10,11-octahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrole (Example 1A, compound 1A-a) (220.0 mg, 0.90 mmol) and paraformaldehyde (810 mg, 2.7 mmol) were stirred in methanol (10 mL) at rt for 30 min. NaBH3CN was added and stirring was continued for 30 min. The mixture was quenched with 1N NaOH (10 mL), extracted with CH2Cl2 (20 mL×4). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo providing 230.1 mg (98.9%) of the title compound 1B as a white solid.

Workup

  1. customThe mixture was quenched with 1N NaOH (10 mL)
  2. extractionextracted with CH2Cl2 (20 mL×4)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e5cb187bf1145f9a5613b06b38b1e39
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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