Formaldehyde → HCID 86705583, compound

HRID 2279603Notes

Reaction equation

HRID 2279603 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:11][NH:10][CH2:9][C@H:8]2[OH:12])=[CH:4][C:3]=1[F:15].C=O.[BH3-][C:19]#N.[Na+]>CO>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:11][N:10]([CH3:19])[CH2:9][C@H:8]2[OH:12])=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86705584HCID 86705584, compound

Product 1

HCID 86705583HCID 86705583, compoundYield 222.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 420 (0.35 g, 1.52 mmol) and MeOH (5 mL) was added HCHO (37% in water, 0.42 mL, 15.2 mmol). The mixture was stirred at RT for 2 h and then NaCNBH3 (1.43 g, 22.8 mmol) was added. The reaction was stirred at RT for 3 h. The reaction was quenched with aqueous NH4OH (50 mL) and the mixture was extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (3×50 mL), dried (Na2SO4) and concentrated in vacuo to afford 0.830 g of cis-(±)-4-(4-chloro-3-fluorophenoxy)-1-methylpyrrolidin-3-ol as a brown oil (422) which used for next step without further purification: LC-MS (ESI) m/z 246 (M+H).

Workup

  1. stirringThe reaction was stirred at RT for 3 h
  2. customThe reaction was quenched with aqueous NH4OH (50 mL)
  3. extractionthe mixture was extracted with EtOAc (3×10 mL)
  4. washThe combined organic phases were washed with water (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ca6c3b8165b4827b4467984505779ba
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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