Formaldehyde → HCID 67507506, compound

HRID 1791909Notes

Reaction equation

HRID 1791909 reaction equation
[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([C@@H:14]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([N:28]3[CH2:32][CH2:31][S:30][CH2:29]3)=[O:27])[CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.Cl.N(C1CCN([C@@H]2CN[C@H](C(N3CCSC3)=O)C2)CC1)[C:37]1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCCl.O.C(O)(=O)C>[C:22]([O:21][C:19]([N:17]1[CH2:18][C@@H:14]([N:11]2[CH2:10][CH2:9][CH:8]([N:1]([CH3:37])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)[CH2:15][C@H:16]1[C:26]([N:28]1[CH2:32][CH2:31][S:30][CH2:29]1)=[O:27])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67507042HCID 67507042, compoundHCID 67507215HCID 67507215, compound

Product 1

HCID 67507506HCID 67507506, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-[(2S,4S)-4-(4-Anilinopiperidino)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 148 (3), 1.18 g] was dissolved in 1,2-dichloroethane (75 mL), and sodium triacetoxyborohydride (5.32 g), acetic acid (0.73 mL) and 37% formaldehyde solution (5.0 mL) were added thereto. The mixture was stirred at room temperature for 12 hr. The reaction mixture was added to water, 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 column chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(N-methylanilino)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (967 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe extract was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7d395d8b4204e2f810e2e993877d9bd
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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