Formaldehyde → HCID 53679684, compound

HRID 1416618Notes

Reaction equation

HRID 1416618 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=O)(C)(C)C.C(OC(N1CCC[C@@H]1CO)=O)(C)(C)C.C=O>C(O)=O>[CH3:6][N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 53986037HCID 53986037, compound

Product 1

HCID 53679684HCID 53679684, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 376 mg (1.2 mmol) sample of 3-((1-t-butoxycarbonyl-2-(R)-pyrrolidinyl)methoxy)-6-chloropyridine, prepared from (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol by the procedure described in Example 45a above, was treated with paraformaldehyde and formic acid for 2 hours as described in Example 16a above. The crude material was purified by column chromatography on silica gel, eluting with 20:1 chloroform:methanol to afford 219 mg of the title compound. MS (DCI/NH3) m/e: 225/227 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.07 (s, 1H), 7.25-7.18 (m, 2H), 4.02 (dd, J=9.1, 5.4 Hz, 1H), 3.93 (dd, J=9.1, 5.4 Hz, 1H), 3.17-3.11 (m, 1H), 2.71-2.67 (m, 1H), 2.49 (s, 3H), 2.38-2.29 (m, 1H), 2.10-1.98 (m, 1H), 1.91-1.68 (m, 3H). [α]25D =+64.5° (c=1.1, CHCl3).

Workup

  1. customThe crude material was purified by column chromatography on silica gel
  2. washeluting with 20:1 chloroform

Sources & evidence

ORD record
ord-5468503eb1934994b98ea662540a28f7
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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