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Nitrogen → (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chloro-5-fluorophenyl)methyl)piperidine-1-carboxylate

HRID 2039901
Notes
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Reaction equation

HRID 2039901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([O:23][CH2:24][C:25]#[N:26])[C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:6]([F:8])[CH:7]=1.N#N.B.S(C)C>C1COCC1>[NH2:26][CH2:25][CH2:24][O:23][C@@H:9]([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 947NitrogenHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 67365681(R)-tert-butyl 3-((R)-(3-chloro-5-fluorophenyl)(cyanomethoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 58017392(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chloro-5-fluorophenyl)methyl)piperidine-1-carboxylateYield 26.4%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (R)-tert-butyl 3-((R)-(3-chloro-5-fluorophenyl)(cyanomethoxy)methyl)piperidine-1-carboxylate (90 g) in anhydrous THF (1.3 L), under protection of N2, was heated to reflux followed by the dropwise addition of 10 M H3B.SMe2 in THF (70 mL, 0.7 mol). The mixture was stirred at reflux overnight. The reaction was quenched with MeOH (500 mL) and the solvent removed in vacuo, the residue was purified by column chromatography to give (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chloro-5-fluorophenyl)methyl)piperidine-1-carboxylate (24 g, 0.062 mol).

Workup

  1. temperatureto reflux
  2. temperatureat reflux overnight
  3. customThe reaction was quenched with MeOH (500 mL)
  4. customthe solvent removed in vacuo
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e380da6d58f542369016e66ca9cd69d1
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580823B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes