Formaldehyde → HCID 69060576, compound

HRID 1984300Notes

Reaction equation

HRID 1984300 reaction equation
Cl.[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[C:9]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:24](C)=O.[Na+]>ClC(Cl)C>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[C:9]([N:3]1[CH2:4][C@@H:5]2[CH2:8][C@H:2]1[CH2:7][N:6]2[CH3:24])=[O:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69001664HCID 69001664, compound

Product 1

HCID 69060576HCID 69060576, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (S,S)-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-(1H-indol-2-yl)-methanone hydrochloride (50 mg, 0.18 mmol), TEA (50 μL, 0.36 mmol), and formaldehyde (6 μL, 0.22 mmol) in dichloroethane (DCE)/MeOH (10:1, 3 mL) was added NaB(OAc)3H (115 mg, 0.54 mmol). After 2 h at rt, the mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were washed with satd aq. NaCl, dried (Na2SO4), and concentrated to yield an orange solid (44 mg, 96%). MS (ESI): mass calcd. for C15H17N3O, 255.14; m/z found, 256.4 [M+H]+. 1H NMR (mixture of rotamers; CDCl3): 10.34-10.08 (m, 1H), 7.64-7.54 (m, 1H), 7.44-7.35 (m, 1H), 7.24-7.16 (m, 1H), 7.09-7.00 (m, 1H), 6.80 (s, 0.5H), 6.67 (s, 0.5H), 4.99-4.86 (m, 1H), 4.05-3.95 (m, 0.7H), 3.84-3.77 (m, 0.3H), 3.71-3.62 (m, 1H), 3.55-3.46 (m, 1H), 3.18-3.10 (m, 0.3H), 2.98-2.88 (m, 0.7H), 2.82-2.69 (m, 1H), 2.46-2.31 (m, 3H), 1.98-1.88 (m, 1H), 1.79-1.70 (m, 1H).

Workup

  1. additionthe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2 (3×)
  3. washThe combined organic layers were washed with satd aq. NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b71e1a4a6744cb9842105eaa96b5dec
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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