HCID 59598521, compound → HCID 59598503, compound

HRID 2266236Notes

Reaction equation

HRID 2266236 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([C@:14]([C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]3)([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([C:5]1[O:6][C:7]2[C:13]([C@:14]([C@@H:22]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 59598521HCID 59598521, compound

Product 1

HCID 59598503HCID 59598503, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(R)-tert-butyl 3-((S)-1-(2-tert-butylbenzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (250 mg, 0.53 mmol) was dissolved in 20% TFA/CH2Cl2 (4 mL). The reaction mixture was stirred at rt for 1 h. The mixture was quenched with satd aq NaHCO3 (15 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4. The filtrate was evaporated to give a residue, which was purified by preparative HPLC to afford pure (S)-1-(2-tert-butylbenzofuran-7-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (185 mg, 94%). 1H NMR (CDCl3): 0.95 (s, 1), 1.24 (m, 2H), 1.36 (s, 9H), 1.49 (m, 3H), 1.64 (m, 2H), 2.02 (m, 2H), 2.55 (m, 2H), 2.82 (s, 1H), 3.1 (s, 1H), 3.25 (m, 5H), 3.66 (m, 1H), 6.35 (s, 1H), 7.18 (t, 1H), 7.28 (d, 1H), 7.42 (d, 1H), 8.96 (s, 1H), 9.33 (s, 1H)

Workup

  1. customThe mixture was quenched with satd aq NaHCO3 (15 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customThe filtrate was evaporated
  5. customto give a residue, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-77c57b9b4be64d3eb30bcecb1edf77fa
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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