Formaldehyde → HCID 67507858, compound

HRID 1829104Notes

Reaction equation

HRID 1829104 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[C:30]#[N:31])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[C:34]([C@@H]1CCCN1C([C@@H]1C[C@H](NCC2C=CC(C#N)=CC=2)CN1)=O)#N.C=O.C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH3:34])[CH2:10][C@H:9]1[C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[C:30]#[N:31])=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67506711HCID 67506711, compoundHCID 67507082HCID 67507082, compound

Product 1

HCID 67507858HCID 67507858, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

(S)-1-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylmethyl)amino-2-pyrrolidinylcarbonyl]-2-cyanopyrrolidine [product of Example 31 (1), 1.04 g] and 37% formaldehyde solution (0.7 mL) were dissolved in acetonitrile (15 mL), and the mixture was stirred at room temperature for 1 hr. Sodium cyanoborohydride (0.240 g) and acetic acid (0.4 mL) were added to the reaction mixture, and the mixture was stirred for 1 hr. The reaction mixture was evaporated under reduced pressure. Saturated aqueous sodium hydrogencarbonate solution was added to the residue and the mixture was extracted with chloroform. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give (S)-1-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-methylamino]-2-pyrrolidinylcarbonyl}-2-cyanopyrrolidine (0.71 g) as amorphous.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionSaturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. customThe extract was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-201ef2541997403e92e7df766fcef988
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

Loading…