Acetic Acid → HCID 69332948, compound

HRID 354521Notes

Reaction equation

HRID 354521 reaction equation
[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:14]([O:18][C:19]([N:21]([CH2:23][CH:24]=O)[CH3:22])=[O:20])([CH3:17])([CH3:16])[CH3:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]([CH2:24][CH2:23][N:21]([C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:20])[CH3:22])[CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 23511873Ethyl 3-fluoro-4-piperidineacetate

Product 1

HCID 69332948HCID 69332948, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-fluoro-4-piperidinylacetate (230 mg, 1.22 mmol) and 2-(N-tert-butoxy carbonyl-N-methylamino)acetaldehyde (211 mg, 1.22 mmol) in THF (5 mL) was added NaBH(OAc)3 (386 mg, 1.82 mmol) and acetic acid (70.0 mL, 1.22 mmol) at room temperature After being sired for 24 hr, the reaction mixture was quenched by the addition of sat. NaHCO3 solution and extracted with EtOAc. The extracts were washed with brine, dried over Na2CO3, and concentrated to dryness. Chromatography of the residue with CHCl3—MeOH (6:1, v/v) as eluent gave ethyl 3-fluoro-1-[2-(N-tert-butoxycarbonyl-N-methylamino)ethyl]-4-piperidinylacetate (236 mg, 56%) as a reddish oil. 1H-NMR (CDCl3) δ1.25 (t, J=7.1 Hz, 3H), 1.45 (s, 9H), 1.53 1.79 (m, 2H), 1.90-2.09 (m, 2H), 2.15 (dd, J=16.4, 7.1 Hz, 1H), 2.45-2.58 (m, 2H), 2.87 (s, 3H), 2.90-2.99 (m, 2H), 3.20 (m, 1H), 3.24-3.45 (m, 2H), 4.14 (q, J=7.1 Hz, 2H), 4.61, 4.73 (each broad s, 1H); ESI-MS m/z 347.

Workup

  1. customthe reaction mixture was quenched by the addition of sat. NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried over Na2CO3
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-599198aac41e487bbe0a2c3d403c080b
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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