Pyrrolidine → HCID 22728989, compound

HRID 2085131Notes

Reaction equation

HRID 2085131 reaction equation
COC[O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=O)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.P(C#N)(OCC)(OCC)=O>>[OH:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 76257Diethyl cyanophosphonateHCID 22728980HCID 22728980, compound

Product 1

HCID 22728989HCID 22728989, compoundYield 92%

Procedure

By the reactions in the same manner as in Starting Material Synthesis Example 16 using 4-(methoxymethyloxy)-benzo(b)thiophene-2-carboxylic acid (3.0 g), pyrrolidine (0.75 g) and diethyl cyanophosphate (2.5 g), 1-(4-hydroxybenzo(b)-thiophene-2-carbonyl)pyrrolidine (2.4 g) was obtained as a brown oil. By the reactions in the same manner as in Starting Material Synthesis Example 1 using the brown oil (2.0 g) and (S)-glycidyl nosylate (2.0 g), the title compound (0.45 g) was obtained as brown crystals.

Sources & evidence

ORD record
ord-40ee68c4c3984f799e75583f7b035dbd
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

Loading…