Methyl cyclopent-1-ene-1-carboxylate → HCID 86607904, compound

HRID 736807

Reaction equation

HRID 736807 reaction equation
[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]1([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25][CH2:24][CH:23]=1.CC1(C)[C@]23C4(ON4S(=O)(=[O:39])C2)C[C@H]1CC3>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]([C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[C@@H:23]1[CH2:24][CH2:25][CH2:26][C@:22]1([OH:39])[C:27]([O:29][CH3:30])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 549129Methyl cyclopent-1-ene-1-carboxylateHCID 1268086(+)-BenzylphenethylamineHCID 16212283(1R,8R)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxideHCID 178418339Butyllithium

Product 1

HCID 86607904HCID 86607904, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

According to the procedure of Tet. Asymm., 13, 2002, 1555: To a solution of (R)-N-benzyl-N-α-methylbenzylamine (1.37 mL, 2 eq.) in THF (10 mL) at −78° C. was added n-butyllithium (2.4 M, 2.2 mL, 1.6 eq). The reaction was allowed to stir for 30 min at −78° C. and then methyl 1-cyclopentene-1-carboxylate (0.41 mL, 3.25 mmol, 1 eq) was added dropwise. The reaction was stirred for 3 h at −78° C. and then a solution of (1R)-(−)-(10-camphorsulfonyl)oxaziridine (1.49 g, 2 eq) in THF (12 mL) was added dropwise via cannula. The reaction was allowed to stir at room temperature overnight, and was then taken up in ethyl acetate, washed with NaHCO3 (1×), brine (2×), dried over Na2SO4, filtered and concentrated. Purification by silica chromatography eluting with a gradient of 10-15% ethyl acetate/hexanes afforded methyl (1R,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-hydroxycyclopentanecarboxylate as an off white solid (0.77 g, 69%). MS: 354.2 (M+H)+

Workup

  1. stirringThe reaction was stirred for 3 h at −78° C.
  2. stirringto stir at room temperature overnight
  3. washwashed with NaHCO3 (1×), brine (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica chromatography
  8. washeluting with a gradient of 10-15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6692c222604a422190905e5c5ec97def
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Linked notes

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