Piperidine → HCID 58597303, compound

HRID 1444711Notes

Reaction equation

HRID 1444711 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([CH:19]=O)=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:19][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 58597271HCID 58597271, compound

Product 1

HCID 58597303HCID 58597303, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ((R)-2,2,2-trifluoro-N-(6-formyl-7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (350 mg, 1.1 mmol) in 6 mL of 1,2-dichloroethane was added piperidine (187 mg, 2.2 mmol) and NaBH(OAc)3 (350 mg, 1.65 mmol). After stirring at RT overnight, the reaction was quenched with Sat. NaHCO3, extracted with EtOAc, dried over Na2SO4, filtered, and evaporated to dryness. Flash chomatography (SiO2, EtOAc/hexane=1:1) afforded (R)-2,2,2-trifluoro-N-(7-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide as a white solid.

Workup

  1. customthe reaction was quenched with Sat. NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c6ccabb370c24e9ebbd519855aff8770
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…