Formaldehyde → HCID 67507506, compound

HRID 1829117Notes

Reaction equation

HRID 1829117 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-77299c9a640c4cd4b571fc18e2a8141d
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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